Ever since Evan sang a heartfelt song to Carlin and asked her to "officially court," they've been inseparable. Two years later, they're both more than ready to take the next step in their relationship. Unbeknownst to Carlin, he has a fairytale proposal plan in the works for his leading lady. After surprising her at a Nashville recording studio, the young couple, along with their parents, head off to Portland, Maine for a fun getaway. The young couple head out for a scenic bike ride to a picturesque picnic spot by the bay! But when Evan and Carlin get lost during their ride, will his perfect proposal plan be in jeopardy? And later, the proposal countdown begins! It's a mad rush for Kelly Jo, Gil and Evan's mom to help Evan put his plan in motion...but more importantly, will Carlin say, "Yes", when Evan woos her with a hand-written poem, a ballroom dance and her favorite diamond ring?